Objectives: This study aims to provide insight into educational differences in duration of working life by working life expectancy (WLE) and working years lost (WYL) through disability benefits and other non-employment states in the Netherlands. Methods: Monthly information on employment status of the Dutch population (N=4 999 947) between 16 and 66 years from 2001‒2015 was used to estimate working life courses and loss of working years for specific non-employment states. Across educational groups, bi-directional transitions between paid employment and non-employment states were calculated. Using a multistate model, the WLE and WYL at age 16, 30, 50 and up to 66 years as statutory retirement age were estimated for each educational group, stratified by gender. Results: Low-educated men and women had a 7.3 (men) and 9.9 (women) years lower WLE at age 30 than high-educated men and women. Among low-educated men, 3.4 working years were lost due to disability benefit compared to 0.8 among high-educated men. Low-educated women lost 3.0 working years due to disability benefit compared to 1.4 among high-educated women. Conclusions: There are large educational inequalities over the course of working life. Among low-educated workers, more working years are lost due to unemployment, no income, and especially disability benefits. The latter reflects large educational inequalities in health and working conditions. The metrics of WLE and WYL provide useful insights into the life-course perspective on working careers.